400747-98-0

Basic information

• Product Name: 4'-TRIFLUOROMETHYL-BIPHENYL-3-YLAMINE
• Synonyms: AKOS BAR-0123;4'-(TRIFLUOROMETHYL)[1,1'-BIPHENYL]-3-AMINE;4'-TRIFLUOROMETHYL-BIPHENYL-3-YLAMINE;3-[4-(Trifluoromethyl)phenyl]aniline;4'-(Trifluoromethyl)-biphenyl-3-amine
• CAS NO: 400747-98-0
• Molecular Formula: C₁₃H₁₀F₃N
• Molecular Weight: 237.22
• Mol File: 400747-98-0.mol

Chemical Properties

• Boiling Point: 330.9 °C at 760 mmHg
• Flash Point: 147.9 °C
• Appearance: /
• Density: 1.245 g/cm³
• CAS DataBase Reference: 4'-TRIFLUOROMETHYL-BIPHENYL-3-YLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-TRIFLUOROMETHYL-BIPHENYL-3-YLAMINE(400747-98-0)
• EPA Substance Registry System: 4'-TRIFLUOROMETHYL-BIPHENYL-3-YLAMINE(400747-98-0)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 400747-98-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4'-TRIFLUOROMETHYL-BIPHENYL-3-YLAMINE is used as a building block for the synthesis of various biologically active compounds and molecules. Its unique molecular structure and properties contribute to the development of a wide range of therapeutic products.
Used in Agrochemical Industry:
In the agrochemical industry, 4'-TRIFLUOROMETHYL-BIPHENYL-3-YLAMINE serves as a key intermediate in the production of agricultural products, aiding in the synthesis of molecules with pesticidal or herbicidal properties.
Used in Research and Development:
4'-TRIFLUOROMETHYL-BIPHENYL-3-YLAMINE is utilized as a reagent or catalyst in chemical reactions, facilitating the development of new compounds and processes in the scientific community. Its unique properties make it a promising candidate for advancing research in various chemical fields.

Upstream product

• 128796-39-4 4-trifluoromethylphenylboronic acid 
• 591-19-5 m-Bromoaniline 
• 626-01-7 3-Iodoaniline 
• 122924-26-9 3--2-cyclohexen-1-one 
• 1453494-27-3 C₁₃H₁₂F₃NO 

Downstream Products

• 637352-75-1 ethyl [2-methyl-4-({pentyl[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}sulfonyl)phenoxy]acetate 
• 637352-76-2 ethyl [4-({(2-cyclopropylethyl)[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}sulfonyl)-2-methylphenoxy]acetate 
• 637352-74-0 ethyl [4-({butyl[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}sulfonyl)-2-methylphenoxy]acetate 
• 637352-73-9 ethyl [2-methyl-4-({(propylsulfonyl)[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)phenoxy]acetate 
• 637352-61-5 ethyl [4-({(2-cyclopropylethyl)[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)-2-methylphenoxy]acetate 
• 637352-60-4 ethyl [2-methyl-4-({pentyl[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)phenoxy]acetate 
• 637352-72-8 ethyl [4-({butyryl[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)-2-methylphenoxy]acetate 
• 637352-58-0 ethyl [4-({butyl[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)-2-methylphenoxy]acetate 
• 637352-59-1 ethyl [4-({(2-methoxyethyl)[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)-2-methylphenoxy]acetate 
• 637352-64-8 methyl [2-methyl-4-({[2-(methylthio)ethyl][4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)phenoxy]acetate 
• 637353-20-9 ethyl [2-ethyl-4-({[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)phenoxy]acetate 

Relevant articles and documents

Lipid peroxidation inhibition study: A promising case of 1,3-di([1,1′-biphenyl]-3-yl)urea

In the present study eighteen inhibitors of the hydrolytic enzymes of the endocannabinoid system were investigated for antioxidant activity using lipid peroxidation (LP) method. Among the assayed compounds ten belong to carbamates with phenyl [1,1′-biphenyl]-3-ylcarbamate (6), reported for the first time, and eight are retro-amide derivatives of palmitamine. Interestingly, results indicated that most of the tested compounds have good antioxidant properties. In particular, 1,3-di([1,1′-biphenyl]-3-yl)urea (3) shows IC50 = 26 ± 6 μM comparable to ones obtained for standard antioxidants trolox and quercetin (IC50 = 22 ± 6 μM and 23 ± 6 μM, respectively). Compound 3 was investigated further by means of DFT calculations, to clarify a possible mechanism of the antioxidant action. In order to estimate the capability of 3 to act as radical scavenger the structure was optimized at B3LYP/6–311++G** level and the respective bond dissociation enthalpies were calculated. The calculations in non-polar medium predicted as favorable mechanism a donation of a hydrogen atom to the free radical and formation of N-centered radical, while in polar solvents the mechanism of free radical scavenging by SPLET dominates over HAT H-abstraction. The possible radical scavenging mechanisms of another compound with potent antioxidant properties (IC50 = 53 ± 12 μM), the retro-amide derivative of palmitamine (compound 18), was estimated computationally based on the reaction enthalpies of a model compound (structural analogue to 18). The computations indicated that the most favorable mechanisms are hydrogen atom transfer from the hydroxyl group in meta-position of the benzamide fragment in nonpolar medium, and proton transfer from the hydroxyl group in ortho-position of the benzamide fragment in polar medium.

From alkylarenes to anilines via site-directed carbon–carbon amination

Anilines are fundamental motifs in various chemical contexts, and are widely used in the industrial production of fine chemicals, polymers, agrochemicals and pharmaceuticals. A recent development for the synthesis of anilines uses the primary amination of C–H bonds in electron-rich arenes. However, there are limitations to this strategy: the amination of electron-deficient arenes remains a challenging task and the amination of electron-rich arenes has a limited control over regioselectivity—the formation of meta-aminated products is especially difficult. Here we report a site-directed C–C bond primary amination of simple and readily available alkylarenes or benzyl alcohols for the direct and efficient preparation of anilines. This chemistry involves a novel C–C bond transformation and offers a versatile protocol for the synthesis of substituted anilines. The use of O2 as an environmentally benign oxidant is demonstrated, and studies on model compounds suggest that this method may also be used for the depolymerization of lignin.

Aromatic amine compound synthesis method

The invention discloses an aromatic amine compound synthesis method which is characterized in that the method is implemented according to any of two methods. The first method includes the steps: mixing an alkyl aromatic compound with a general formula (I) and a nitrogen-containing compound with a general formula (II); performing reaction on mixture under an oxidizing agent and an organic solvent to obtain an aromatic amine compound with a general formula (III). The second method includes the steps: mixing an aromatic alcohol derivative with a general formula (I') and the nitrogen-containing compound with the general formula (II); performing reaction on mixture under an acid additive and an organic solvent to prepare the aromatic amine compound with the general formula (III). According to the method, a lot of alkyl aromatic compounds or aromatic alcohol derivatives firstly serve as raw materials, and the raw materials are reacted to generate the aromatic amine compound without the action of metal catalysis. Compared with a traditional synthesis method, the synthesis method has the advantages that the method is high in yield and simple in condition, waste discharging amount is less,metal participation is omitted, a reaction device is simple, industrial production is easily achieved and the like. The method has a wide application prospect.

Design, synthesis, and structure-activity relationship of 7-propanamide benzoxaboroles as potent anticancer agents

Benzoxaboroles, as a novel class of bioactive molecules with unique physicochemical properties, have been shown to possess excellent antimicrobial activities with tavaborole approved in 2014 as an antifungal drug. Although urgently needed, the investigation of benzoxaboroles as anticancer agents has been lacking so far. In this study, we report the design, synthesis, and anticancer structure-activity relationship of a series of 7-propanamide benzoxaboroles. Compounds 103 and 115 showed potent activity against ovarian cancer cells with IC50 values of 33 and 21 nM, respectively. Apoptosis was induced by these compounds and colony formation was effectively inhibited. Furthermore, they also showed excellent efficacy in ovarian tumor xenograft mouse model.

Design, synthesis, molecular modelling and in vitro cytotoxicity analysis of novel carbamate derivatives as inhibitors of Monoacylglycerol lipase

Monoacylglycerol lipase (MAGL) has an essential role in the catabolic pathway of the endocannabinoid 2-arachidonoylglycerol, which makes it a potential target for highly specific inhibitors for the treatment of a number of diseases. We designed and synthesized a series of carbamate analogues of URB602. We evaluated their inhibitory activity toward human MAGL in vitro both in cell culture and lysates. The target compounds exhibited moderate to excellent inhibitory activity against MAGL. The most promising compound 2b showed good inhibitory activity with IC50 value of 4.5 ± 0.70 μM reducing MAGL activity to 82% of controls at 10 μM compared to 66% for the parent compound URB602. Interestingly, compounds 2b and 2c induce cell death through the inhibition of MAGL. Molecular modelling approaches and docking studies, used to investigate inhibitory profiles, indicated that trifluoromethyl substitutions of the aryl group and the benzene ring present at the oxygen side of the carbamate molecule had a significant impact on the activity.

Pd-catalyzed Semmler-Wolff reactions for the conversion of substituted cyclohexenone oximes to primary anilines

Homogeneous Pd catalysts have been identified for the conversion of cyclohexenone and tetralone O-pivaloyl oximes to the corresponding primary anilines and 1-aminonaphthalenes. This method is inspired by the Semmler-Wolff reaction, a classic method that exhibits limited synthetic utility owing to its forcing conditions, narrow scope, and low product yields. The oxime N-O bond undergoes oxidative addition to Pd0(PCy3)2, and the product of this step has been characterized by X-ray crystallography and shown to undergo dehydrogenation to afford the aniline product.

PROCESS FOR PRODUCING BIARYL COMPOUND

A method for producing a biaryl compound, comprising reacting an aromatic organic compound with at least one compound selected from the group consisting of aromatic organoboron compounds and boroxine compounds, in the presence of a zero-valent nickel catalyst, phosphine ligand and base.

Compounds, compositions and methods

Compounds useful for treating cellular proliferative diseases and disorders by modulating the activity of KSP are disclosed.

Novel ATP-competitive kinesin spindle protein inhibitors

Kinesin spindle protein (KSP), an ATPase responsible for spindle pole separation during mitosis that is present only in proliferating cells, has become a novel and attractive anticancer target with potential for reduced side effects compared to currently available therapies. We report herein the discovery of the first known ATP-competitive inhibitors of KSP, which display a unique activity profile as compared to the known loop 5 (L5) allosteric KSP inhibitors that are currently under clinical evaluation. Optimization of this series led to the identification of biphenyl sulfamide 20, a potent KSP inhibitor with in vitro antiproliferative activity against human cells with either wild-type KSP (HCT116) or mutant KSP (HCT116 D 130V). In a murine xenograft model with HCT116 D130V tumors, 20 showed significant antitumor activity following intraperitoneal dosing, providing in vivo proof-of-principle of the efficacy of an ATP-competitive KSP inhibitor versus tumors that are resistant to the other known KSP inhibitors.

Compounds, Compositions and Methods

Compounds useful for treating cellular proliferative diseases and disorders by modulating the activity of KSP are disclosed.